#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/18/7121839.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7121839
loop_
_publ_author_name
'Wang, Miao'
'Tang, Bo-Cheng'
'Wang, Jun-Gang'
'Xiang, Jia-Chen'
'Guan, Ao-Yu'
'Huang, Ping-Ping'
'Guo, Wu-Yinzheng'
'Wu, Yan-Dong'
'Wu, An-Xin'
_publ_section_title
;
 The triple role of rongalite in aminosulfonylation of aryldiazonium
 tetrafluoroborates: synthesis of N-aminosulfonamides via a radical
 coupling reaction.
;
_journal_issue                   55
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7641
_journal_page_last               7644
_journal_paper_doi               10.1039/c8cc03778g
_journal_volume                  54
_journal_year                    2018
_chemical_formula_sum            'C14 H16 N2 O2 S'
_chemical_formula_weight         276.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-04-26 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.902(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.955(3)
_cell_length_b                   5.5629(19)
_cell_length_c                   12.732(4)
_cell_measurement_reflns_used    1421
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.66
_cell_volume                     704.2(4)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0909
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            1887
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.048
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       Block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.243
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1842
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.243
_refine_ls_R_factor_all          0.1102
_refine_ls_R_factor_gt           0.0975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2489
_refine_ls_wR_factor_ref         0.2910
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_full    0.973
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                1580
_reflns_number_total             1842
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc03778g2.cif
_cod_data_source_block           1_a
_cod_depositor_comments          'Adding full bibliography for 7121839.cif.'
_cod_database_code               7121839
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.960
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.8566(13) 0.624(3) 0.4241(8) 0.077(4) Uani 1 1 d . .
H1A H 0.8666 0.7958 0.4222 0.116 Uiso 1 1 calc R U
H1B H 0.8216 0.5681 0.3569 0.116 Uiso 1 1 calc R U
H1C H 0.9426 0.5513 0.4403 0.116 Uiso 1 1 calc R U
C2 C 0.7584(6) 0.5556(10) 0.5097(4) 0.054(2) Uani 1 1 d G .
C3 C 0.6832(7) 0.3453(9) 0.5022(4) 0.056(3) Uani 1 1 d G .
H3 H 0.6945 0.2393 0.4468 0.067 Uiso 1 1 calc R U
C4 C 0.5910(6) 0.2932(9) 0.5774(4) 0.053(2) Uani 1 1 d G .
H4 H 0.5407 0.1525 0.5724 0.064 Uiso 1 1 calc R U
C5 C 0.5742(5) 0.4515(11) 0.6602(4) 0.043(2) Uani 1 1 d G .
C6 C 0.6494(5) 0.6618(10) 0.6677(3) 0.047(2) Uani 1 1 d G .
H6 H 0.6382 0.7677 0.7231 0.056 Uiso 1 1 calc R U
C7 C 0.7416(5) 0.7138(9) 0.5925(4) 0.049(2) Uani 1 1 d G .
H7 H 0.7919 0.8545 0.5975 0.059 Uiso 1 1 calc R U
C8 C 0.2266(5) 0.5191(10) 0.8581(4) 0.046(2) Uani 1 1 d G .
C9 C 0.1229(6) 0.5974(10) 0.7893(4) 0.056(3) Uani 1 1 d G .
H9 H 0.1344 0.7339 0.7484 0.068 Uiso 1 1 calc R U
C10 C 0.0021(5) 0.4719(13) 0.7814(5) 0.067(3) Uani 1 1 d G .
H10 H -0.0673 0.5243 0.7353 0.080 Uiso 1 1 calc R U
C11 C -0.0150(5) 0.2680(12) 0.8424(5) 0.051(2) Uani 1 1 d G .
C12 C 0.0887(6) 0.1896(10) 0.9112(4) 0.055(2) Uani 1 1 d G .
H12 H 0.0772 0.0532 0.9521 0.066 Uiso 1 1 calc R U
C13 C 0.2095(5) 0.3152(11) 0.9191(4) 0.052(2) Uani 1 1 d G .
H13 H 0.2788 0.2628 0.9651 0.063 Uiso 1 1 calc R U
C14 C -0.1475(12) 0.133(3) 0.8355(10) 0.086(4) Uani 1 1 d . .
H14A H -0.2031 0.1876 0.8902 0.130 Uiso 1 1 calc R U
H14B H -0.1308 -0.0359 0.8437 0.130 Uiso 1 1 calc R U
H14C H -0.1925 0.1624 0.7682 0.130 Uiso 1 1 calc R U
N1 N 0.4786(7) 0.3981(17) 0.7359(5) 0.053(2) Uani 1 1 d . .
H1 H 0.4111 0.3062 0.7203 0.064 Uiso 1 1 calc R U
N2 N 0.4967(8) 0.4969(15) 0.8353(5) 0.049(2) Uani 1 1 d . .
H2 H 0.5657 0.4644 0.8761 0.059 Uiso 1 1 calc R U
O1 O 0.4095(8) 0.7264(18) 0.9797(5) 0.074(3) Uani 1 1 d . .
O2 O 0.3732(7) 0.8726(13) 0.7969(6) 0.0634(19) Uani 1 1 d . .
S1 S 0.3791(2) 0.6782(5) 0.86984(14) 0.0487(8) Uani 1 1 d . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C3 C2 C7 120.0
C3 C2 C1 121.1(6)
C7 C2 C1 118.8(6)
C4 C3 C2 120.0
C4 C3 H3 120.0
C2 C3 H3 120.0
C3 C4 C5 120.0
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.0
C6 C5 N1 120.5(5)
C4 C5 N1 119.5(5)
C7 C6 C5 120.0
C7 C6 H6 120.0
C5 C6 H6 120.0
C6 C7 C2 120.0
C6 C7 H7 120.0
C2 C7 H7 120.0
C9 C8 C13 120.0
C9 C8 S1 120.4(3)
C13 C8 S1 119.6(3)
C10 C9 C8 120.0
C10 C9 H9 120.0
C8 C9 H9 120.0
C11 C10 C9 120.0
C11 C10 H10 120.0
C9 C10 H10 120.0
C12 C11 C10 120.0
C12 C11 C14 119.8(7)
C10 C11 C14 120.1(7)
C11 C12 C13 120.0
C11 C12 H12 120.0
C13 C12 H12 120.0
C12 C13 C8 120.0
C12 C13 H13 120.0
C8 C13 H13 120.0
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N2 N1 C5 118.5(6)
N2 N1 H1 120.7
C5 N1 H1 120.7
N1 N2 S1 115.7(6)
N1 N2 H2 122.2
S1 N2 H2 122.2
O2 S1 O1 119.4(5)
O2 S1 N2 107.5(4)
O1 S1 N2 105.0(4)
O2 S1 C8 108.7(4)
O1 S1 C8 108.3(4)
N2 S1 C8 107.2(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.548(11)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.3900
C2 C7 1.3900
C3 C4 1.3900
C3 H3 0.9300
C4 C5 1.3900
C4 H4 0.9300
C5 C6 1.3900
C5 N1 1.419(8)
C6 C7 1.3900
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.3900
C8 C13 1.3900
C8 S1 1.757(5)
C9 C10 1.3900
C9 H9 0.9300
C10 C11 1.3900
C10 H10 0.9300
C11 C12 1.3900
C11 C14 1.516(13)
C12 C13 1.3900
C12 H12 0.9300
C13 H13 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
N1 N2 1.383(9)
N1 H1 0.8600
N2 S1 1.623(8)
N2 H2 0.8600
O1 S1 1.441(6)
O2 S1 1.425(7)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C7 C2 C3 C4 0.0
C1 C2 C3 C4 -177.0(7)
C2 C3 C4 C5 0.0
C3 C4 C5 C6 0.0
C3 C4 C5 N1 179.2(6)
C4 C5 C6 C7 0.0
N1 C5 C6 C7 -179.2(6)
C5 C6 C7 C2 0.0
C3 C2 C7 C6 0.0
C1 C2 C7 C6 177.0(7)
C13 C8 C9 C10 0.0
S1 C8 C9 C10 -179.3(5)
C8 C9 C10 C11 0.0
C9 C10 C11 C12 0.0
C9 C10 C11 C14 178.9(8)
C10 C11 C12 C13 0.0
C14 C11 C12 C13 -178.9(8)
C11 C12 C13 C8 0.0
C9 C8 C13 C12 0.0
S1 C8 C13 C12 179.3(5)
C6 C5 N1 N2 -25.4(9)
C4 C5 N1 N2 155.4(6)
C5 N1 N2 S1 117.4(7)
N1 N2 S1 O2 -60.4(7)
N1 N2 S1 O1 171.4(7)
N1 N2 S1 C8 56.3(7)
C9 C8 S1 O2 -2.8(5)
C13 C8 S1 O2 177.9(4)
C9 C8 S1 O1 128.3(5)
C13 C8 S1 O1 -51.0(6)
C9 C8 S1 N2 -118.8(4)
C13 C8 S1 N2 61.9(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 786403
